1-(4-chlorophenyl)-2-methylpropan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-chloro-α-isopropylbenzyl alcohol (33.08 g) in 48% hydrobromic acid (330 mL) is stirred at room temperature for 1 hour and extracted with hexanes. The combined organic extracts are washed sequentially with water, saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a yellow oil (42.98 g) which is identified by NMR spectral analysis. extracted with hexanes The combined organic extracts are washed sequentially with water, saturated sodium hydrogen carbonate solution and water dried over anhydrous sodium sulfate concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 M solution of p-chlorophenylmagnesium bromide in diethyl ether (100 mL) is added to a solution of isobutyraldehyde (9.08 mL, 0.1 mol) in diethyl ether at −5° C. After the addition is complete, the reaction mixture is stirred overnight at room temperature, diluted with an ice-water mixture, and acidified with 10% hydrochloric acid. The phases are separated and the aqueous phase is extracted with diethyl ether. The organic phase and extracts are combined, washed sequentially with saturated sodium hydrogen carbonate solution, water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a 33% methylene chloride in hexanes solution gives the title product as a colorless oil (14 g) which is identified by NMR spectral analyses. After the addition The phases are separated the aqueous phase is extracted with diethyl ether washed sequentially with saturated sodium hydrogen carbonate solution, water and brine dried over anhydrous sodium sulfate concentrated in vacuo to obtain an oil

Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(4'-Chlorophenyl)-2-methyl-1-propanol (9.6 grams, 0.05 moles), ethanol (4.5 grams, 0.1 mole), and hexane (32 grams) are charged into a 300 cubic centimeter Hastelloy C autoclave. The autoclave is purged twice with nitrogen, evacuated to 100 mm Hg, and cooled to -30° C. Hydrogen fluoride (75 grams, 3.25 mole) is then added and the reactor is pressurized to 600 psig with carbon monoxide. The reaction mass is stirred for about an hour at room temperature. The hydrogen fluoride is vented and the contents are removed and poured onto crushed ice. A solution of 45% potassium hydroxide is added to the mixture until the pH of the mixture is adjusted to 6.0-6.5. The mixture is then extracted with ethyl acetate (3 times with 150 ml of ethyl acetate each time). The combined organic extract is dried with anhydrous magnesium sulfate, filtered, and concentrated to yield the crude product. The crude product is distilled under vacuum to give pure ethyl 2,2-dimethyl-3-(4'-chlorophenyl)propanoate. The autoclave is purged twice with nitrogen evacuated to 100 mm Hg the contents are removed poured onto crushed ice A solution of 45% potassium hydroxide is added to the mixture until the pH of the mixture The mixture is then extracted with ethyl acetate (3 times with 150 ml of ethyl acetate each time) The combined organic extract is dried with anhydrous magnesium sulfate filtered concentrated to yield the crude product The crude product is distilled under vacuum